反应详情

To a solution of 3-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzonitrile (0.117 g, 0.31 mmol) in MeOH (3.0 mL)was added Et3N (0.14 mL, 1.00 mmol) followed by NH2OH.H2O (0.070 g, 1.01 mmol). The resultant mixture was stirred at room temperature overnight. The mixture was diluted with water (5 mL) and extracted with CH2Cl2 (5×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH) provided 113 mg (88%) of COMPOUND 71 as a white solid. 1H NMR (CDCl3) δ 1.50-1.72 (m, 3H), 1.94-2.19 (m, 3H), 2.40 (s, 6H), 3.40 (s, 2H), 3.97 (d, 2H, J=9.3 Hz), 5.75 (br s, 2H), 6.37 (d, 1H, J=7.5 Hz), 6.71 (dd, 1H, J=7.5, 7.5 Hz), 6.89 (dd, 2H, J=7.5, 4.8 Hz), 7.19 (d, 1H, J=8.1 Hz), 7.26-7.29 (m, 2H), 7.42 (s, 1H), 8.30 (d, 2H, J=3.9 Hz); ES-MS m/z 416 (M+H).

1. extractionextracted with CH2Cl2 (5×10 mL)
2. dry with materialThe combined organic extracts were dried (Na2SO4)
3. concentrationconcentrated
4. customPurification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH)